Setting Up Work Structures To Succeed

00:00:00.000 | - All right, Jesse, well, I'm liking the live interaction

00:00:03.420 | we've put into the show.

00:00:04.260 | Last week, we had our friend David Sachs in the studio

00:00:07.300 | helping us answer some questions.

00:00:08.720 | Today, let's take a live call from one of our listeners.

00:00:12.520 | - Yep, we got Phillip here, so let's take a listen.

00:00:15.300 | - All right, Phillip, thanks for calling into the podcast.

00:00:19.700 | What is on your mind today?

00:00:21.180 | - Hey, Cal.

00:00:22.940 | So I've been recently going through a bit of a life shift.

00:00:26.220 | I spent a few years as an entrepreneur

00:00:27.860 | running two venture capital-backed startups.

00:00:30.520 | Then after selling my last company,

00:00:32.500 | I worked in product management roles

00:00:34.800 | at a couple of later stage technology startups

00:00:37.340 | for a few years.

00:00:38.580 | And that was a lot of hyperactive hive mind,

00:00:40.860 | you know, over 100 Slack channels or 30 meetings per week.

00:00:44.080 | A lot of structured what I was working on also, though.

00:00:47.020 | And so now I've split out to start a new company.

00:00:50.180 | And my goal is to build it solo without external funding,

00:00:52.660 | kind of Basecamp style.

00:00:54.480 | And I'm spending about half of my time

00:00:56.120 | doing consulting work to cover costs.

00:00:58.660 | And I'm spending the other half of my time

00:00:59.900 | developing my own in-house products.

00:01:01.980 | The goal is to grow these in-house products and revenue

00:01:03.740 | so I can eventually focus on them more full-time.

00:01:06.980 | And I split out solo because I did some value-based,

00:01:09.220 | lifestyle-centric career planning

00:01:10.940 | and decided that starting a solo product development studio

00:01:13.640 | aligns more with the values and lifestyle

00:01:15.820 | that I wanted to pursue.

00:01:17.540 | So my high-level question is,

00:01:19.220 | how do I apply the principles of slow productivity

00:01:21.300 | and deep life to set myself up for success?

00:01:23.940 | I've gone from a lot of structure to no structure,

00:01:25.980 | and I could use some help

00:01:26.900 | making sure that my habits are sustainable.

00:01:29.160 | - Well, I mean, first of all,

00:01:31.460 | I'm upset that you're not using our acronym for that.

00:01:34.420 | - VBLCCP.

00:01:35.420 | - VBLCCP, yeah.

00:01:36.780 | I mean, this is, we gotta be pithy.

00:01:39.180 | I think we all agree that that rolls off the tongue.

00:01:42.480 | Okay, this is a great question.

00:01:44.640 | Tell me a little bit more, though,

00:01:46.020 | about this studio situation you have set up.

00:01:51.020 | What's that like?

00:01:52.100 | So what's the work gonna be like?

00:01:54.340 | - Yeah, so I'm doing some product development.

00:01:57.580 | So I'm working with a client,

00:01:59.340 | kind of building an entire application,

00:02:01.620 | end to end, including definition and design

00:02:03.660 | and things like that.

00:02:04.740 | And I'm working on a couple of personal projects,

00:02:07.940 | like one of which is the main focus,

00:02:09.300 | already has revenue, already has some customers.

00:02:11.660 | It's not quite revenue to live off of.

00:02:13.940 | This is a path I used to start my previous company,

00:02:16.700 | Moonlight.

00:02:17.540 | So we did some freelancing as we grew the company,

00:02:20.740 | and eventually it grew in size

00:02:23.380 | and raised venture capital

00:02:25.060 | and kind of took a traditional kind of path.

00:02:28.580 | And I think a lot of what I'm trying to do

00:02:29.660 | with this product studio

00:02:30.700 | is also not necessarily trying to pursue

00:02:33.740 | that traditional path.

00:02:34.780 | There's a lot of kind of extrinsic markers of success.

00:02:37.740 | Like you could go raise money and hire employees

00:02:39.620 | and things like that.

00:02:40.620 | I'm trying to be a little bit more controlled about that.

00:02:43.700 | So my day-to-day is really unstructured.

00:02:45.820 | I have full control of my time now.

00:02:47.620 | I have one client meeting per week,

00:02:49.300 | which is a lot less than what I had

00:02:51.580 | at later stage startups.

00:02:53.060 | So I'm tending to break my day

00:02:55.780 | into three, two-hour deep work blocks

00:02:58.940 | with kind of two hours in between each

00:03:00.900 | for a mix of admin work and breaks.

00:03:03.260 | So I guess kind of like a general high-level question

00:03:04.940 | I have is, is this too much or too little deep work

00:03:07.380 | in a given day?

00:03:08.660 | And with more control of my time,

00:03:10.260 | is it better to break up my day more

00:03:11.940 | or to try to keep deep work

00:03:13.620 | and more work, admin work,

00:03:16.700 | focused on more of a traditional kind of nine-to-five slot?

00:03:19.300 | - Yep. All right.

00:03:20.140 | That's a good question.

00:03:20.980 | And we'll get in this nitty gritty.

00:03:22.380 | I wanna underscore first,

00:03:25.340 | I like your decision you made of,

00:03:28.100 | well, let's keep this small.

00:03:30.540 | Have you read Paul Jarvis, "The Company of One"?

00:03:34.540 | - Yeah, I've read part of it.

00:03:35.500 | I don't think I finished it, but it's a good book.

00:03:38.300 | - I mean, you're right in line, I think,

00:03:40.260 | with Paul's thinking here.

00:03:42.540 | If people haven't read that, they should.

00:03:44.820 | It has a blurb for me, so you know that it's quality.

00:03:48.540 | Paul also, he was a designer, I guess.

00:03:50.420 | He was in web design.

00:03:51.540 | And the whole book is about,

00:03:53.500 | instead of expanding your company,

00:03:55.780 | so companies that begin with you and your skill,

00:03:58.100 | instead of expanding it

00:03:59.380 | to hit those intrinsic markers of success,

00:04:01.860 | so size, revenue, then funding,

00:04:03.940 | his whole point is keep it small.

00:04:07.340 | If you get more in demand, you can just charge more

00:04:09.780 | and therefore even work less.

00:04:11.460 | Like actually, it can be a great engine

00:04:13.380 | for a lifestyle that you have a huge amount of autonomy over.

00:04:16.260 | And I think it's a great model.

00:04:18.460 | So in terms of your specific day,

00:04:19.580 | there's no right answer to the exact right way

00:04:23.180 | to move deep work around how many blocks to have.

00:04:26.540 | I have a couple of things I'm gonna throw out there,

00:04:28.780 | a couple of heuristics,

00:04:29.620 | and you can see which of these might stick.

00:04:33.140 | I'm a big believer in these situations

00:04:35.060 | of doing meeting-free Monday and Friday, if you can.

00:04:38.460 | So you just have the scheduling heuristic

00:04:40.340 | that client calls, client meetings,

00:04:43.460 | you know, whatever, I gotta call my accountant,

00:04:45.180 | we gotta, the IT person's upgrading some sort of software,

00:04:47.900 | whatever it is, nothing gets scheduled

00:04:49.980 | for Monday and Fridays.

00:04:52.340 | That alone just changes the character of the week

00:04:55.140 | because it's like you have a four-day weekend,

00:04:57.420 | you're just deep working on Friday,

00:04:59.220 | you're deep working on Monday,

00:05:00.540 | you can really get lost in things.

00:05:02.580 | So I think that can make a big difference.

00:05:05.060 | And then the other thing I might suggest

00:05:06.660 | would be consolidating the deep work.

00:05:10.380 | All right, deep work to lunch, meetings, clients,

00:05:12.820 | administrative stuff in the afternoon.

00:05:15.020 | Trying to keep that together, keep that mindset going,

00:05:19.860 | and not have anything interspersed into that

00:05:22.620 | that's unrelated.

00:05:24.420 | So those are two heuristics I've seen.

00:05:26.100 | Would that graft well onto your current setup?

00:05:28.700 | - Some, yeah.

00:05:30.820 | I really wanted to live more asynchronously

00:05:34.100 | when I started this company,

00:05:35.020 | so I only have one meeting per week normally.

00:05:38.180 | - All right, that's easy.

00:05:39.780 | - Yeah, so that makes it easier,

00:05:40.620 | but that also is a lot more uncertainty

00:05:43.780 | in terms of should every day kind of be the same

00:05:45.900 | or kind of create more texture throughout the week.

00:05:48.420 | But yeah, so you think that kind of training

00:05:52.820 | to do longer periods of deep work is better?

00:05:56.620 | - Yeah, I would do it first thing in the day,

00:05:59.980 | until lunch, maybe just make that be a standard.

00:06:02.820 | And then the other thing I would do,

00:06:04.660 | I mean, you have a very enviable situation here.

00:06:06.620 | You have a huge amount of autonomy

00:06:08.140 | in terms of demands on your time

00:06:10.660 | because of the way you set this up, so congratulations.

00:06:13.740 | This is something I do during the summer.

00:06:15.300 | Like when I'm a professor in the summer,

00:06:16.700 | I'm like you all the time.

00:06:18.020 | So I have many fewer obligations.

00:06:20.260 | My time is very, very open.

00:06:22.180 | And so I have the same concern about how to structure it.

00:06:24.540 | It's deep work in the morning

00:06:26.540 | and then variable but clearly defined shutdowns.

00:06:29.420 | That's another thing I lean into

00:06:30.940 | is I'm gonna time block out my afternoon.

00:06:33.660 | I'll be clear about when my shutdown's

00:06:35.220 | gonna happen this afternoon.

00:06:37.300 | And when I'm shutdown complete,

00:06:38.580 | I'm not working on work anymore.

00:06:40.420 | That can be really early some days, right?

00:06:42.740 | So what this allows you to do is it's Tuesday.

00:06:45.180 | I deep work till lunch and that went really well.

00:06:48.220 | I don't have any particularly

00:06:49.460 | pressing administrative thing.

00:06:50.940 | I'm gonna do a formal schedule shutdown ritual at one o'clock

00:06:54.820 | and because I recognize, hey, this day is done

00:06:56.900 | and I feel good about it,

00:06:58.020 | I can really lean into those other hours to do other things,

00:07:01.540 | completely unrelated to work or whatever.

00:07:03.580 | And then on another day, you said, look,

00:07:04.820 | I got my call with my client

00:07:06.620 | and now I really gotta figure out whatever,

00:07:08.380 | this new software package.

00:07:09.900 | And so this is gonna take me till five

00:07:11.740 | and I'll do the clear shutdown then.

00:07:13.460 | But having the clearly defined shutdown each day,

00:07:16.740 | I mean, allows you to really work with this variable

00:07:18.660 | workflow and take a lot more advantage

00:07:20.540 | of what it gives you.

00:07:22.300 | I mean, maybe you wanna become a cinephile.

00:07:24.220 | It's like, great, two days a week, I'm going to the movies,

00:07:27.380 | the two o'clock show or whatever.

00:07:29.700 | That's the type of thing you can do

00:07:31.140 | when you feel like I shut down,

00:07:33.180 | I feel comfortable shutting down,

00:07:35.620 | I'm looking at my schedule, this is good,

00:07:37.780 | I'm on track for things.

00:07:39.220 | And so now I really have to figure out

00:07:40.620 | what to do with my time.

00:07:42.180 | That's what I might also be concerned about

00:07:43.900 | if I was you, is making sure it's not this hazy mix

00:07:46.060 | of work and non-work guilt in the afternoon.

00:07:49.020 | Like, I don't know, maybe I should go back on email,

00:07:51.060 | what's going on.

00:07:52.660 | Be clear about it, but then be very comfortable

00:07:55.460 | taking advantage of all the advantages you have.

00:07:57.860 | - Okay, great.

00:08:00.740 | Another kind of question along the lines

00:08:02.100 | of slow productivity is, should I work on weekends?

00:08:04.580 | So I'm trying to do some client work and some personal work.

00:08:08.020 | So I am not sure if I should continue working on weekends.

00:08:12.140 | Right now I'm taking one day off per week,

00:08:14.340 | but I think there could be value in getting more done.

00:08:17.140 | So how do you think about working on weekends?

00:08:19.420 | - Would it be the personal project

00:08:21.860 | that you're mainly doing on the weekends?

00:08:23.700 | - Yeah.

00:08:24.980 | - I think it's fine.

00:08:26.180 | I mean, if you have the time and you find it interesting,

00:08:28.820 | I think you're smart to take,

00:08:30.820 | whether it be Saturday or Sunday,

00:08:32.300 | a full day completely off is fine.

00:08:35.860 | But if you're working on a personal project,

00:08:38.060 | I think that's fine.

00:08:38.900 | I typically will write on Sundays, for example.

00:08:41.860 | I don't do any other work on the weekend.

00:08:44.500 | So I'm not gonna do, I'm not gonna do CS work.

00:08:48.660 | Producer Jesse knows I'm probably not gonna answer emails

00:08:51.100 | about issues with the podcast, whatever, but I do write.

00:08:56.100 | Because it's a very personal activity for me.

00:08:58.460 | It's meaningful to me.

00:09:00.580 | It doesn't change me into a mindset

00:09:03.580 | of hyperactive hive mind.

00:09:05.140 | So I think if your personal project

00:09:06.460 | is not throwing you back into a world

00:09:09.260 | of scheduling meetings and sending emails,

00:09:11.940 | but it's coding or is trying to master a new system,

00:09:15.660 | I think that's completely fine.

00:09:16.740 | I mean, if you enjoy it, go for it.

00:09:18.820 | Keep you one day off.

00:09:19.660 | I mean, I think you got this pretty well dialed in here,

00:09:21.460 | Philip, from what I'm hearing.

00:09:22.980 | - So one of the life buckets is community.

00:09:27.140 | I've moved around a lot.

00:09:28.940 | I was a nomad for two years and I'm temporarily

00:09:31.860 | in a new city with my significant others

00:09:33.780 | in grad school.

00:09:35.660 | How do you think community should factor in

00:09:37.780 | for somebody in my situation?

00:09:39.220 | I think there's not a lot of local people

00:09:41.220 | that are in the same situation as me,

00:09:43.180 | but a lot of online communities tend to be more real time,

00:09:48.180 | like Discord or Telegram.

00:09:50.460 | And I don't wanna have those kind of synchronous demands

00:09:54.260 | on my attention.

00:09:55.460 | What do you think is a good way to kind of continue

00:09:57.500 | to have some community?

00:09:58.460 | 'Cause I don't really have that from coworkers

00:10:01.180 | or from kind of other companies in the same situation

00:10:04.780 | through an investor or something like that.

00:10:06.820 | - What city are you in?

00:10:09.020 | - I'm in Chicago.

00:10:10.180 | - Oh, okay.

00:10:11.020 | I mean, I think you should have community involvements.

00:10:16.460 | I think they should have scheduled synchronous demands

00:10:19.700 | on your time, and I think they should be in person.

00:10:22.380 | I think that's an important part of the human condition.

00:10:25.660 | And as I talk about in digital minimalism,

00:10:27.500 | it's actually the non-trivial sacrifice of time

00:10:31.180 | and attention on behalf of other people

00:10:32.580 | that makes that connection something

00:10:33.900 | that's valued by your brain.

00:10:35.700 | And so I would put in that work now.

00:10:39.700 | Now, are you saying your significant other

00:10:41.460 | is in grad school somewhere else,

00:10:42.620 | or you came to Chicago because-

00:10:43.460 | - I'm here.

00:10:44.420 | - Okay, that's good.

00:10:45.300 | - Yeah, we're here in Chicago, she's in school.

00:10:46.780 | I think I agree with what you're saying.

00:10:48.700 | I think what I'm having trouble with is finding peers.

00:10:51.140 | - Oh, that's hard.

00:10:51.980 | - There's a lot of people that are more advanced

00:10:54.260 | or learning from me.

00:10:56.580 | But I think where I find I have issues

00:10:58.340 | is a lot of my kind of peers that I know

00:11:00.980 | are in other cities, not necessarily locally.

00:11:04.460 | - Yeah, well, I mean, I'm saying get entangled

00:11:07.140 | in some community involvement here unrelated to your work.

00:11:10.820 | - Okay, that makes sense.

00:11:12.500 | - Yeah, I mean, it could be through fitness,

00:11:15.140 | it could be through faith, it could be through activity,

00:11:18.100 | whatever, trail running or whatever.

00:11:21.620 | I mean, there's such a wide variety,

00:11:23.460 | but I would anchor myself right away

00:11:26.340 | with, or if you're into, I mentioned movie,

00:11:28.500 | you're into movies, like let me find a club

00:11:30.420 | that meets and does these things.

00:11:32.020 | And that becomes the offshoot of making friends

00:11:35.020 | and people you end up spending time with one-on-one.

00:11:36.580 | I think that's really critical.

00:11:38.340 | I would recognize it's hard, right?

00:11:41.140 | Because we don't have like an app solution for that.

00:11:43.060 | We can't just like swipe a thing

00:11:44.420 | and then like a friend comes over.

00:11:46.860 | But I would put a lot of effort into that,

00:11:48.900 | especially if I'm new to a city.

00:11:50.460 | And you have the time and flexibility to do this.

00:11:52.860 | And I think that's a great investment of the time you have.

00:11:55.700 | - Yeah, I've done a good job of meeting friends

00:11:58.740 | and communities locally,

00:11:59.740 | but I think the thing that I'm finding hardest

00:12:01.260 | kind of being solo is like professional peers

00:12:04.220 | and people that are working on similar problems

00:12:06.260 | and things like that.

00:12:07.540 | So I've considered kind of like setting up

00:12:09.740 | like a mastermind call or something weekly

00:12:12.820 | with some people that are working on similar things here.

00:12:14.660 | I think that's really kind of the main thing

00:12:17.140 | that I'm concerned about is meeting other people

00:12:19.340 | that also think this isn't as crazy

00:12:22.020 | and that are going through kind of similar

00:12:25.380 | professional challenges or things like that.

00:12:28.060 | Yeah. - Yeah, I see what you're saying.

00:12:30.260 | I mean, I think that could be helpful.

00:12:31.660 | Writers have the same issue.

00:12:33.140 | It's a very lonely job.

00:12:35.060 | You don't go to an office and it's weird.

00:12:37.340 | Like most people aren't writers, so it's hard to find.

00:12:40.820 | And I've done something similar.

00:12:41.980 | I've been involved in various writers groups.

00:12:44.580 | I mean, in my sense, the value falls out of those

00:12:47.380 | is not the fact that we're getting together on Zoom

00:12:51.220 | every other week, it's the six months in,

00:12:54.100 | this particular member of the group you kind of connect with

00:12:56.740 | and now there's someone you text with.

00:12:58.100 | Now there's someone that like you see when they're in town.

00:13:00.620 | So I see your question better now.

00:13:03.820 | I would say it's worth it having the,

00:13:06.040 | you talked about the synchronous commitment,

00:13:08.140 | make the commitment.

00:13:08.980 | I think that's fine. - Yeah.

00:13:10.220 | - Get together some groups.

00:13:11.580 | Yeah, they're usually mixed.

00:13:13.500 | These groups are okay, but it's like who you meet

00:13:15.480 | in the group could be pretty valuable.

00:13:17.100 | So I see what you're saying there.

00:13:19.180 | But on the other hand, hey, as a writer,

00:13:21.740 | I can say it is pretty lonely.

00:13:22.860 | I mean, I know other writers, but it's a pretty,

00:13:27.020 | it could be a pretty lonely job and that's just part of it.

00:13:30.440 | So you find connection outside.

00:13:34.860 | I mean, look, I built this studio so I can come hang out

00:13:37.780 | with people because otherwise I'm just writing by myself,

00:13:41.180 | but also having my Georgetown position.

00:13:43.220 | I noticed a really big difference

00:13:45.720 | when the campus opened again, for example, post COVID.

00:13:48.620 | Like, oh, just being able to come here, be around people.

00:13:50.780 | So I think that is really valuable.

00:13:52.020 | It's also just really hard.

00:13:53.020 | I just know a lot of writers who,

00:13:54.580 | some of them meet other writer friends,

00:13:55.980 | but it's a weird job.

00:13:57.420 | Your situation might be similar.

00:13:58.740 | So I think it's worth it to try those groups.

00:14:01.340 | It might help.

00:14:02.180 | You might meet some people,

00:14:03.460 | but I think you need to be okay with the fact

00:14:06.260 | that you may not ever have the same experience

00:14:09.380 | as the other person you know,

00:14:11.780 | who's in the 30 person venture-backed startup

00:14:13.900 | and they're in the office 12 hours a day.

00:14:16.120 | And it's, you know, here's the ping pong table

00:14:18.300 | and we're just getting after it.

00:14:19.380 | You know, it is a little bit more lonely.

00:14:21.380 | I think Paul Jarvis is great about that in that book

00:14:23.500 | because he moved to the middle of nowhere.

00:14:25.540 | I mean, he lives, I don't know, in the woods.

00:14:27.580 | He lives in the woods in British Columbia somewhere,

00:14:30.620 | but they love it, but it's like completely different.

00:14:33.060 | I mean, they're on their own

00:14:34.900 | if they're doing their own thing.

00:14:36.420 | And so you can be happy with that too.

00:14:38.540 | So I basically am validating your pain here, Philip.

00:14:40.780 | It is hard and you can probably,

00:14:42.700 | you might be able to do better,

00:14:44.060 | but I don't want to sugar coat it.

00:14:45.560 | Like when you do a solo-preneur type situation like this,

00:14:49.460 | I think a lot of your community connection

00:14:50.820 | comes outside of work.

00:14:53.140 | - Yeah.

00:14:54.060 | How do you think about coaches?

00:14:56.300 | I think coaching is kind of having a moment right now

00:14:58.820 | and I've had some friends recommend

00:15:00.100 | hiring like a professional coach.

00:15:02.140 | I think that also kind of factors into accountability

00:15:04.620 | that on some of the client projects,

00:15:06.620 | I feel like I can be working harder for someone else

00:15:08.860 | than I work for myself.

00:15:10.340 | Do you think, like, how do you think about coaching?

00:15:12.680 | - I think you should try it.

00:15:13.900 | Yeah, do a six month engagement

00:15:15.900 | that like, this is what we're trying.

00:15:17.560 | So it's more like you re-up,

00:15:18.980 | not that you would have to actually cancel it yourself

00:15:21.180 | to see if it's a good fit or not.

00:15:22.620 | I have a coach.

00:15:23.500 | It is someone, she specializes in dealing with creatives

00:15:29.300 | who also are struggling with the issues

00:15:31.340 | of the business side of being a creative.

00:15:32.980 | So, I mean, it is a very narrow expertise

00:15:35.720 | that I need a lot of help on.

00:15:38.440 | So she works with writers and filmmakers

00:15:41.820 | and screenwriters and directors

00:15:43.500 | and where businesses build up

00:15:46.340 | around their creative endeavors.

00:15:47.780 | And I found that to be really useful.

00:15:50.580 | So I would say I'm on board with coaching.

00:15:52.500 | Not every coach is gonna be a fit.

00:15:54.540 | So try it out, but absolutely invest in that

00:15:58.200 | because you can get a huge return on that investment

00:16:01.540 | if it really changes the way you think about your business,

00:16:03.940 | the way you think about your life.

00:16:05.860 | So yeah, you got my stamp of approval on that.

00:16:07.780 | I think there should be more coaching in general.

00:16:10.180 | And I think you're right, it's having a moment

00:16:12.620 | where people are realizing I do a high-end job.

00:16:15.940 | There's a lot at stake.

00:16:16.900 | It's complicated.

00:16:18.600 | There's huge dividends to get in my life

00:16:20.260 | if I could make big changes.

00:16:21.540 | I don't quite know how to do that.

00:16:22.820 | If there's someone who can help me through that,

00:16:24.580 | it could massively change the trajectory of my life.

00:16:26.980 | I'll hire a trainer, I'll hire a doctor,

00:16:28.920 | I'll hire all these other things.

00:16:29.880 | Why am I not hiring someone that's gonna work

00:16:31.460 | on probably the most important thing I do,

00:16:33.060 | which is sort of figuring out exactly

00:16:34.460 | how my career unfolds.

00:16:35.780 | So yeah, you got my approval on that one too.

00:16:38.620 | - Awesome, thanks a lot.

00:16:40.220 | - Great, well, Philip, thanks for calling in.

00:16:41.980 | I think it was a good case study

00:16:42.860 | and a good constellation of related questions.

00:16:45.700 | So definitely keep us posted on how things are going

00:16:48.220 | for you there in Chicago.

00:16:49.860 | - Will do, thanks, Kyle. - All right, thanks.

00:16:51.540 | (upbeat music)

00:16:54.120 | (upbeat music)

Setting Up Work Structures To Succeed

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